Water-soluble reactive organic dyestuffs and processes for their manufacture

摘要

The invention comprises water-soluble reactive dyes of general formulae in which F is the radical of a water-soluble oxazine, dioxazine, triphenylmethane, thioxanthrone, nitro, benzanthrone, dibenzanthrone, naphthalene tetracarboxylic acid, prylenetetracarboxylic acid, a metalliferous azo, anthraquinone or phthalocyanine dyestuff, A is a direct linkage or a bivalent aliphatic bridge member which may contain hetero atoms, R and R1 each represent hydrogen atoms or a substituted or unsubstituted alkyl radicals of 1-4 carbon atoms or an aralkyl radical, X is -SO2-, -CO-, or -CO-NH-, Y is a substituent, Z is an inorganic or organic radical which is capable of being split off by an alkali to give a vinylsulphonylamino group, n is 0, 1 or 2 and m is 1, 2 or 3. The dyes are made by reacting a compound of general formula with a compound of general formulae in which X1 is a carboxylic acid halide, sulphonic acid halide or an isocyanate group, Y1Z, R1 and n being as above, the reaction being in weakly acid, neutral or weakly alkaline medium at pH values of 3-8, preferably at 0-40 DEG C. The dyes provide red, blue, green, and black shades on natural, regenerated or synthetic materials.ALSO:Intermediate acid halides and isocyanates of formulae in which X1 is a carboxylic or sulphonic acid halide group or an isocyanate group, Y is a substituent, Z is a group which is split off by alkalies to give a vinyl-sulphonylamino group, R1 is hydrogen or a substituted or unsubstituted alkyl group of 1-4 carbon atoms and n is 0, 1 or 2, are prepared by: (a) reacting aminobenzenecarboxylic acids or -sulphonic acids with acylating agents which introduce the vinylsulphonic acid radical; (b) by esterifying the b -hydroxy group in isothionylaminobenzenecarboxylic or sulphonic acids with, e.g. acetic acid anhydride or methane sulphonic acid chloride; (c) by allowing vinylsulphonylaminobenzene-carboxylic acids or sulphonic acids to react with e.g. phenols or dialkylamines to give the corresponding b -phenoxy or b -dialkylamino compounds which latter may be quaternized with alkylating agents. The benzenecarboxylic and sulphonic acids obtained in (a), (b) and (c) may be alkylated at the nitrogen atom with dimethyl or diethyl sulphate and then converted in known manner to the corresponding acid halide. The sulphonic acid chlorides may also be produced by diazotizing the aniline derivatives of formulae and reacting the diazonium compound with sulphur dioxide in acetic acid in presence of copper chloride. The isocyanate compounds are obtained by reacting the aniline derivatives above with phosgene in known manner whereby the amino group is changed to isocyanate.